Dean and Sam stayed at the bunker for a few more days before heading out. They had to look for a crossroads demon, but they decided not to go too far. They drove a couple of hours north and got started.
Lily stayed at the bunker. She helped Kevin with the tablet, and waited to hear from Dean. Her surprise was evident when he was back late that night, alone. She and Kevin were at a table in the library. Dean came in, kissed Lily, and sat in a chair next to her.
"What's going on? Where's Sam?"
"He wouldn't let me go with him," Dean said. "Said he had to do this alone."
"What's he doing alone?"
"We found a rogue reaper who smuggles souls out of Hell. He's gonna smuggle Sam in."
"Are you serious?"
"I wish I wasn't."
"And you let him go alone?"
"What was I supposed to do?"
Lily stared at Dean before her gaze fell to the floor. "I don't know... How does he know which soul is innocent? How will he find it?"
"That's..." Dean hesitated. He wasn't sure he wanted to tell Lily. She had taken Bobby's death so hard, and now she was pregnant. He didn't want her upset.
"What, Dean?"
"The reaper said that he was the one who reaped Bobby."
"Okay?"
"He took Bobby to Hell."
"What? That's not right. Bobby doesn't deserve to be there."
"I know. Sam's gonna get him out."
"How does Sam get out? This reaper got him in... does he get him out, too?"
"Yeah. He gave Sam twenty-four hours. I have to go back tomorrow night."
"Well," Lily said, "I know you won't sleep, but you should rest." She rubbed her hand over his back, and across his shoulders. "Why don't we go to bed?"
"That sounds good," he said with a smile.
They made Kevin close the books and head to the sleeping quarters. Dean showered, then met Lily in their room. He climbed into bed next to her, and kissed her gently. She snuggled up to his side as he lay back, and put her hand on his bare chest. Her fingers lightly brushed over his skin.
"Try to sleep," she said. "Okay?"
"I'll try."
Lily eventually drifted off to sleep, but she awoke a few hours later when Dean bolted upright in the bed. Lily rubbed the sleep from her eyes as she watched Dean practically jump out of the bed and pull on a shirt and jeans.
"What's wrong?"
"I just got psychically touched by an angel."
"What?"
"Naomi... She came to me in a dream or something. Cas did that to me once before."
"What did she say?"
"That we want the same thing. That she's trying to protect the angel tablet... and that the reaper's way into Hell is through Purgatory."
Lily sat up at the mention of Purgatory. "What are you gonna do?"
"I have to talk to that reaper," he said as he sat to tie up his boot laces.
Lily threw the covers back and got out of bed. "I'm going with you."
"No, you're not," Dean said. His head shot up, his laces momentarily forgotten.
"Sam could be stuck in Hell or Purgatory, and you might need backup."
"Lily, we've talked about this. You agreed."
"I know, but this is a special circumstance," she said as she dressed. "I'm still a hunter, Dean. Don't forget that."
"Trust me, I haven't."
"Good."
Lily grabbed her jacket and left Dean behind to finish with his laces. She told Kevin she was going with Dean, and not to leave the bunker.
As Dean and Lily walked to the car, he grabbed her arm and stopped. She could see the worry on his face, but she couldn't let him go alone. Dean's hand slid down her arm until her hand was in his. He squeezed it gently.
"You realize," he said, "that we're dealing with Hell, here? This is Crowley's territory. If he has any idea what we're doing, he'll be around."
Lily hesitated. She could go the rest of her life without ever seeing Crowley again, and the memories of her time with him would still torment her. The scars on her body had faded, but the mental scars would always be there.
"I understand," she said, "but this is important. We have to make sure Sam is safe. And we have to make sure Bobby gets to Heaven... and not just because of the trial."
With her hand still in his, they walked to the car. A few hours later they pulled up behind a taxi in an alley.
"Stay in the car," Dean told Lily. She didn't argue.
She watched as Dean carefully approached the driver side, and she saw his face fall. He stood there, staring, and Lily couldn't take it. She got out of the car, but stood behind the open door.
"What's wrong?"
"He's dead."
"Was it Crowley?"
"I don't know."
Dean began to pace next to the taxi. When he started walking further down the alley she called out to him.
"Just... wait there," he said. "Get back in the car."
She reluctantly got back in as he pulled out his cell phone. When he came back a few minutes later, his face was both sad and worried.
"Who did you call?"
"Benny."
"Benny... the vampire?"
"Yeah. I told him I need a favor."
"What kind of fav-" Lily's eyes grew wide as she realized what Dean wanted. "Dean..."
"It's the only way. He'll never find the portal on his own."
"Benny agreed?"
"It's not really the kind of thing you ask over the phone. I didn't say what the favor was. He's not too far from here. He's heading our way."
Lily ran her hand through Dean's hair and rubbed at the back of his neck. "If he agrees... can you do it?"
Dean's head dropped forward as his eyes watered. "I have to."
They found a diner that was open for breakfast while they waited. Neither of them really felt like eating, but Dean made Lily eat for the baby. She told him she would eat if he did, so they both sat picking at their food.
Later, back in the alley, they met up with Benny. Dean asked Lily to stay in the car, and she watched their exchange. Benny seemed different than the last time she saw him. He seemed worn and tired. She watched as their faces changed expressions. Finally, Dean walked to the car and reached through the window to grab his machete. He walked back to Benny and extended his hand. Benny took it, and they embraced. As Dean reached back with the blade, Lily turned her head, unable to watch. Dean put Benny's body in the trunk, then got behind the wheel. He sat there a moment, unmoving. Lily couldn't fight the tears that fell. She moved next to Dean and took his face in her hands, pressing kisses to his lips and cheeks.
"I'm so sorry," she whispered.
After a moment, Dean pulled away and started the ignition. "We have to go to Maine. That's where the portal leads."
Dean broke every speed limit getting to Maine. They walked for over an hour through dense forest until he found the area he thought was the right place. Then they waited. It wasn't very long before a bright light filled the air and Sam came walking through the trees. Dean went to him and hugged him tight.
"Purgatory, right? A real garden spot, ain't it?"
"Yeah," Sam said.
"Did you get him out?"
"Only Bobby."
"What? I mean, that's fantastic about Bobby..."
"Dean, look... Benny, uh... he got us out. A bunch of vamps showed and he used himself as bait. I get the feeling that even if that didn't happen, he didn't wanna come back, you know? I'm sorry."
"You're probably right," Dean said. Lily grabbed his hand with a supportive squeeze. "So, uh... Bobby," Dean said. "How'd he hold up down there?"
"He's good, all things considered. Ornery as hell, of course."
"As he should be. Let's put that old man where he belongs."
Sam recited the incantation and sliced open his arm were Bobby was being held. They all watched as his spirit, bathed in a white light, went upward toward the sky, until it was suddenly surrounded by a swirling cloud of black and red.
"What the hell," Dean asked.
"Hello, boys." They all turned to see Crowley. He looked up at the scene above him. "Bobby Singer... I'd know you anywhere."
"Let him go, Crowley," Dean said. "He doesn't belong in Hell."
"He does if I say he does. He's inflicted untold damage on my kind. From where I sit, actually, Hell's too good for him."
Sam and Dean tried to rush Crowley, but a flick of his index finger sent them flying through the air until they were pinned against two large tree trunks, where they hung several feet off of the ground. Lily stood there, eyes wide, unsure of her next move. She couldn't afford to be slammed into a tree with he baby. Crowley's voice drew her attention back.
"Well, if it isn't my favorite playmate," he said. "I have missed you."
"Get away from her, Crowley," Dean yelled.
"Or what? You'll shout me to death?" He smiled at Lily as he lifted her hand to his mouth, and she fought the urge to vomit. He pushed the sleeve of her jacket up. "No scars, I see. Doesn't that earn me some points?" Lily remained quiet, but her eyes were set on him like daggers. "I grew quite fond of you, you know. And I think you were beginning to feel the same way. You leaned into my touch."
"I was physically weak... and I was thinking of someone else."
"Well... that's disappointing."
Crowley struck Lily across the face, and she let out a cry. Dean struggled, in vain, to free himself.
"You son-of-a-bitch! I'll kill you."
Crowley just grinned and looked up at Bobby, bringing him back down, but something interfered. Naomi was suddenly standing between Crowley and Lily.
"Oh, come on," Crowley groaned.
"Let me see if I've interpreted the situation correctly," Naomi said. "The Winchesters have freed an innocent from Hell, to which you are wrongfully trying to return it."
"Siding with them, Naomi? You don't know those two. Before they're done, we'll both be locked away."
"I'm just hoping they lock you away, dear. The rest I'll figure out."
"Bureaucrat. You're fighting outside your weight class."
"Don't call me a bureaucrat."
A bright light radiated from within Naomi as she held her hand out toward Crowley, and he disappeared. Dean and Sam fell from their places against the trees, and Lily ran to Dean. Naomi then pointed toward the sky, releasing Bobby's spirit. They all watched as it disappeared into the night sky.
"I told you you could trust me," Naomi said to Dean. Then she was gone.
"What the hell was that about," Sam asked.
"I'll tell you later. Let's get this trial done."
Sam pulled a small piece of paper from his pocket and read the incantation. He fell to the ground in pain, holding his arm.
"Sam? What? What? Talk to me! What?" Dean's voice was panicked, and he grabbed Sam's shoulder.
"It's okay! It's okay! I'm fine. It's done."
Lily stooped down and ran her hand over Sam's back, but her eyes went to Dean. He shook his head and leaned to help Sam off of the ground.
"Let's go home," Dean said.
Lily fell asleep in the back seat. She woke up as Dean lifted her into his arms.
"Shhh," he said, "I got you."
Lily put her arms around his shoulders and nuzzled into his neck. Sam held the door open for them and Dean took her straight to their room, closing that door with his foot. He laid her on the bed and lay next to her, brushing his thumb over the forming bruise on her cheek. Her eyes fluttered open.
"How's Sam," she asked.
"He seems to be okay. You okay?"
"I'm okay... Are you?"
"I'm fine. What did Crowley say to you?"
"He was just trying to mess with my head."
"Yeah, I get that. What did he say?"
"That he misses me."
"Bastard... You do realize that you're confined to the bunker now, right?"
"Dean-"
"I mean it, Lily. That was too close."
"Okay... I don't wanna fight."
Dean pulled Lily into his arms, and they both fell asleep.